Research Seminar –
Carbon-nitrogen bonds are ubiquitous across nearly all classes of chemicals from pharmaceuticals to commodity chemicals. An appealing way to incorporate nitrogen into compounds is through the use of nitrenes since they are single N atom units with diverse reactivity. An ideal way to access nitrenes would be from a stable and abundant N-source that has desired functionality incorporated on the N-atom, such as N-aryl or N-alkyl. The nitro group (RNO2) exemplifies this idea, as it is easily installed and nitroarenes and -alkanes can be rapidly derivatized via traditional chemical methods. Recently, a photochemical 1,3-cycloaddition between nitroarenes and alkenes was reported that generates a 1,3,2-dioxazolidine intermediate which then decomposes to oxidatively cleave the alkene. One possible pathway of decomposition generates an aryl nitrene. This proposal aims to develop a research program centered around using a 1,3-cycloaddition between nitro groups and olefin activators to generate nitrenes that can engage in subsequent transformations.